Isolation and characterization of homoisoflavonoids from Scilla persica HAUSSKN

Abstract

Medicinal plants have many traditional claims including the treatment of ailments of infectious origin. In the evaluation of traditional claims, scientific research is extremely important. In this study, five homoisoflavonoids named 3-(4'-hydroxybenzylidene)-5,7-dihydroxy-6-methoxychroman-4-one(Autumnalin),3-(4'-hydroxybenzyl)-5,7-dihydroxy-6-methoxychroman-4-one (3,9-dihydro-autumnalin), 3-(3',4'-dihydroxybenzyl)-5,8-dihydroxy-7-methoxychroman-4-one,3-(3',4'-dihydroxybenzylidene)-5,8-dihydroxy-7-methoxychroman-4-one and 3-(3',4'-dihydroxybenzylidene)-5,7-dihydroxy-6-methoxychroman-4-one, were isolated from the bulbs of the plant Scilla persica HAUSSKN. Their structures were established on the basis of extensive spectroscopic analyses such as NMR, MS, IR and UV.

The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae (sensu APGII)

“…The MeOH and butanol extracts of the bulbs of Eucomis autumnalis yielded compounds 22 and 30−39, and the EtOH extract of the bulbs of E. bicolor yielded compounds 40 and 41. Compounds 31 and 32 have been isolated previously from both E. autumnalis and E. bicolor, 26 compound 36 from E. autumnalis, 27−29 compounds 30, 40, and 41 from E. bicolor, 27,30,31 compound 33 from E. montana, 32 compound 38 from Muscari armeniacum, 17 compound 39 from Scilla persica, 33 and compound 37 from Ledebouria ovatifolia. 23 Compound 35, 3R-(4′-hydroxybenzyl)-6,8-dihydroxy-5,7dimethoxy-4-chromanone, is a homoisoflavonoid that has not been reported previously with a fully substituted ring A. HRMS showed a protonated molecular ion at m/z 347.11254 corresponding to a molecular formula of C 18 H 18 O 7 .…”

“…The MeOH and butanol extracts of the bulbs of Eucomis autumnalis yielded compounds 22 and 30 – 39 , and the EtOH extract of the bulbs of E. bicolor yielded compounds 40 and 41 . Compounds 31 and 32 have been isolated previously from both E. autumnalis and E. bicolor , compound 36 from E. autumnalis , − compounds 30 , 40 , and 41 from E. bicolor , ,, compound 33 from E. montana , compound 38 from Muscari armeniacum , compound 39 from Scilla persica , and compound 37 from Ledebouria ovatifolia …”

A review on traditionally used South African medicinal plants, their secondary metabolites and their potential development into anticancer agents

“…These showed low to moderate activity with IC50 values of 74.6 and 30.5 µM for autumnalin and 3,9-dihydro-autumnalin respectively. Additionally, both these compounds showed moderate toxicity against normal human fibroblasts, both with IC50 values of 100 µM (Ebrahimi et al, 2015). Due to the highly toxic effects seen in animals when the plant was ingested, further studies should be done on the isolation of compounds which could potentially show less toxicity in non-tumorigenic models while having significant activity against cancer cells.…”

Biochemical and biophysical properties of a novel homoisoflavonoid extracted from Scilla persica HAUSSKN

“…It is known as a foodstuff and important plant in traditional medicine for promoting blood circulation, reducing inflammation, as an analgesic [2], and antibacterial agent [3]. Previous studies on Scilla species revealed triterpenoid [4], stilbenoids [5] and cardiac glycosides [6] as well as homoisoflavanones [7][8][9][10][11], which showed antibacterial and anti-angiogenic activities, and inhibited in vitro the growth and sporogenesis of several microorganisms [7,8,11,12].…”